Synthesis and characterization of branched-chain derivatives of methyl oleate

Clean - Soil, Air, Water

Volumn 36, Issue 8, 2008, Pages 687-693

  Dailey Jr , Oliver D ^a   Prevost, Nicolette T ^a   Strahan, Gary D ^b  

^a SOUTHERN REGIONAL RESEARCH CENTER   (United States)

^b EASTERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

Branched chain fatty acids; Differential scanning calorimetry (DSC); Low temperature properties; NMR; Organocuprate reagents

Indexed keywords

BIOFUEL; CALORIMETRY; CHEMOSYNTHESIS; FATTY ACID; GAS CHROMATOGRAPHY; LOW TEMPERATURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; RECRYSTALLIZATION; VEGETABLE OIL;

GOSSYPIUM HIRSUTUM; MICROPUS;

EID: 70349605787     PISSN: 18630650     EISSN: 18630669     Source Type: Journal    
DOI: 10.1002/clen.200800058     Document Type: Article

References (21)

1. G. Knothe, R. O. Dunn, M. O. Bagby, Biodiesel: the Use of Vegetable Oils and Their Derivatives as Alternative Diesel Fuels, in ACS Symp. Ser. 666 (Fuels and Chemicals from Biomass), American Chemical Society, Washington 1997, 172-208.
2. R. O. Dunn, Thermal Analysis of Alternative Diesel Fuels from Vege- table Oils, J. Am. Oil Chem. Soc. 1999, 76, 109-115.
3. I. Lee et al., Use of Branched-Chain Esters to Reduce the Crystalliza- tion Temperature of Biodiesel, J. Am. Oil Chem. Soc. 1995, 72, 1155-1160.
4. T. A. Foglia et al., Low-Temperature Properties of Alkyl Esters of Tal- low and Grease, J. Am. Oil Chem. Soc. 1997, 74, 951-955.
5. W.-H. Wu et al., Low-Temperature Property and Engine Performance Evaluation of Ethyl and Isopropyl Esters of Tallow and Grease, J. Am. Oil Chem. Soc. 1998, 75, 1173-1178.
6. T. A. Isbell et al., Characterization of Estolides Produced from the Acid-Catalyzed Condensation of Oleio Acid, J. Am. Oil Chem. Soc. 1994, 71,379-383.
7. S. C. Cermak et al., Synthesis of Estolides from Oleic and Saturated Fatty Acids, J. Am. Oil Chem. Soc. 2001, 78, 557-565.
8. S. C. Cermak et al., Synthesis and Physical Properties of Estolide- based Functional Fluids, Ind. Crops Prod. 2003, 18, 183-196.
9. S. C. Cermak et al., Synthesis and Physical Properties of Estolides from Lesquerella and Castor Fatty Acid Esters, Ind. Crops Prod. 2006, 23, 54-64.
10. U. Biermann et al., New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry, Angew. Chem. Int. Ed. 2000, 39, 2206-2224.
11. U. Biermann et al., Alkylation of Alkenes: Ethylaluminum-Sesqui- chloride-Mediated Hydro-Alkyl Additions with Alkylchoroformates and Di-tert-butylpyrocarbonate, J. Am. Chem. Soc. 2004, 126, 10319-10330.
12. O. D. Dailey, Jr. et al., Conversion of Methyl Oleate to Branched- Chain Derivatives, J. Am. Oil Chem. Soc. 2007, 84, 565-571.
13. E. J. Corey et al., Selective Formation of Carbon-Carbon Bonds between Unlike Groups Using Organocopper Reagents, J. Am. Chem. Soc. 1967, 89, 3911-3912.
14. E. J. Corey et al., Carbon-Carbon Bond Formation by Selective Cou- pling of n-Alkylcopper Reagents with Organic Halides, J. Am. Chem. Soc. 1968, 90, 5615-5616.
15. W. C. Still et al., Rapid Chromatographic Techniques for Preparative Separation with Moderate Resolution, J. Org. Chem. 1978, 43, 2923-2925.
16. E. Ucciani et al., Sur l'halogenation en position allylique des chaines grasses monoinsatutees. V. Isomerie de place et de position des chaines mono- et dihalogenees, Bull. Soc. chim. France 1963, 28-32.
17. G. Stork et al., The Stereochemistry of the SN29 Reaction. II, J. Am. Chem. Soc. 1956, 78, 4609-4619.
18. R. J. Anderson et al., Stereoselective Synthesis of Olefins. Reactions of Dialkylcopper-Lithium Reagents with Allylic Acetates, J. Am. Chem. Soc. 1970, 92, 735-737.
19. E. E. van Tamelen et al., Synthesis of Cecropia Juvenile Hormone from trans, trans-Farnesol, J. Am. Chem. Soc. 1970, 92, 737-738.
20. D. E. Dorman et al., Carbon-13 Nuclear Magnetic Resonance Spectro- scopy, Quantitative Correlations of the Carbon Chemical Shifts of Acyclic Alkenes, J. Org. Chem. 1971, 36, 2757-2766.
21. N. D. Fernandes et al., A Newly Identified Methyl-branched Fatty Acid Synthesizing Enzyme from Mycobacterium tuberculosis var. bovis BCG, J. Biol. Chem. 1998, 273, 2823-2828.